DE69801590T2 - Imidazolderivate und ihre verwendung als farnesylproteintransferase inhibitoren - Google Patents

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Publication number

DE69801590T2

DE69801590T2 DE69801590T DE69801590T DE69801590T2 DE 69801590 T2 DE69801590 T2 DE 69801590T2 DE 69801590 T DE69801590 T DE 69801590T DE 69801590 T DE69801590 T DE 69801590T DE 69801590 T2 DE69801590 T2 DE 69801590T2

Authority

DE

Germany

Prior art keywords

fluorophenyl

benzoylamino

4alkyl

imidazol

fluorophenethyl

Prior art date

1997-10-22

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 13
• 239000003528 protein farnesyltransferase inhibitor Substances 0.000 title description 4
• 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 181
• 238000000034 method Methods 0.000 claims abstract description 66
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 58
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
• 239000001257 hydrogen Substances 0.000 claims abstract description 42
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 41
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
• 150000003839 salts Chemical class 0.000 claims abstract description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
• 239000000651 prodrug Substances 0.000 claims abstract description 19
• 229940002612 prodrug Drugs 0.000 claims abstract description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 16
• 239000012453 solvate Substances 0.000 claims abstract description 15
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
• 150000001413 amino acids Chemical class 0.000 claims abstract description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 7
• 239000003814 drug Substances 0.000 claims abstract description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 230000008569 process Effects 0.000 claims abstract description 5
• 125000000686 lactone group Chemical group 0.000 claims abstract 2
• -1 C3−6cycloalkyloxy Chemical group 0.000 claims description 126
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 238000006243 chemical reaction Methods 0.000 claims description 47
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
• 125000006239 protecting group Chemical group 0.000 claims description 24
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 22
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 13
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
• 150000002431 hydrogen Chemical group 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 125000000335 thiazolyl group Chemical group 0.000 claims description 10
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 9
• 230000015572 biosynthetic process Effects 0.000 claims description 9
• 201000010099 disease Diseases 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 230000006126 farnesylation Effects 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 5
• 230000001404 mediated effect Effects 0.000 claims description 5
• QZFTYDKBCZOAEF-XLTVJXRZSA-N methyl (2s)-2-[[2-(4-fluorophenyl)-4-[[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]methyl]benzoyl]amino]-4-methylsulfanylbutanoate Chemical compound C1=C(C=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC)=CC=C1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 QZFTYDKBCZOAEF-XLTVJXRZSA-N 0.000 claims description 5
• KPHBTAFAPMFPEM-UXMRNZNESA-N (2s)-2-[[2-(4-fluorophenyl)-6-[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]pyridine-3-carbonyl]amino]-4-methylsulfanylbutanoic acid Chemical compound N1=C(C=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(O)=O)=CC=C1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1 KPHBTAFAPMFPEM-UXMRNZNESA-N 0.000 claims description 4
• SDQPMMOUEUTPEA-PMCHYTPCSA-N (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[2-(3-methylimidazol-4-yl)-1-(1,3-thiazol-2-yl)ethoxy]benzoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(O)=O)=CC=1OC(C=1SC=CN=1)CC1=CN=CN1C SDQPMMOUEUTPEA-PMCHYTPCSA-N 0.000 claims description 4
• MRQSVPHQPKHPEZ-CYZZXXEPSA-N CSCC[C@H](NC(=O)c1ccc(COC(Cc2cncn2C)c2ccc(F)cc2)cc1-c1ccc(F)cc1)C(=O)OC(C)(C)C Chemical compound CSCC[C@H](NC(=O)c1ccc(COC(Cc2cncn2C)c2ccc(F)cc2)cc1-c1ccc(F)cc1)C(=O)OC(C)(C)C MRQSVPHQPKHPEZ-CYZZXXEPSA-N 0.000 claims description 4
• 238000010511 deprotection reaction Methods 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• PLJBTBZJDFCJPL-UFXYQILXSA-N methyl (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]benzoyl]amino]-4-methylsulfanylbutanoate Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC)=CC=1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1 PLJBTBZJDFCJPL-UFXYQILXSA-N 0.000 claims description 4
• SHMAWEDZJRJERX-PMCHYTPCSA-N methyl (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[2-imidazol-1-yl-1-(1,3-thiazol-2-yl)ethoxy]benzoyl]amino]-4-methylsulfanylbutanoate Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC)=CC=1OC(C=1SC=CN=1)CN1C=CN=C1 SHMAWEDZJRJERX-PMCHYTPCSA-N 0.000 claims description 4
• 150000004702 methyl esters Chemical class 0.000 claims description 4
• MLKDQMCDDBVTHP-UFXYQILXSA-N tert-butyl (2s)-2-[[2-(4-fluorophenyl)-4-[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]benzoyl]amino]-4-methylsulfonylbutanoate Chemical compound C1=C(C=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCS(C)(=O)=O)C(=O)OC(C)(C)C)=CC=C1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1 MLKDQMCDDBVTHP-UFXYQILXSA-N 0.000 claims description 4
• PYVNSNSSCLJMPR-JEFWXSHNSA-N tert-butyl (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[1-(4-fluorophenyl)-2-(3-methylimidazol-4-yl)ethoxy]benzoyl]amino]-4-methylsulfanylbutanoate Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC(C)(C)C)=CC=1OC(C=1C=CC(F)=CC=1)CC1=CN=CN1C PYVNSNSSCLJMPR-JEFWXSHNSA-N 0.000 claims description 4
• NOPCWOGPHHJKTQ-JEFWXSHNSA-N tert-butyl (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[1-(4-fluorophenyl)-2-(3-methylimidazol-4-yl)ethoxy]benzoyl]amino]-4-methylsulfonylbutanoate Chemical compound CN1C=NC=C1CC(C=1C=CC(F)=CC=1)OC(C=C1C(=O)N[C@@H](CCS(C)(=O)=O)C(=O)OC(C)(C)C)=CC=C1CCC1=CC=C(F)C=C1 NOPCWOGPHHJKTQ-JEFWXSHNSA-N 0.000 claims description 4
• BPWJCZOINCRLCY-MBMZGMDYSA-N tert-butyl (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[2-imidazol-1-yl-1-(1,3-thiazol-2-yl)ethoxy]benzoyl]amino]-4-methylsulfanylbutanoate Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC(C)(C)C)=CC=1OC(C=1SC=CN=1)CN1C=CN=C1 BPWJCZOINCRLCY-MBMZGMDYSA-N 0.000 claims description 4
• NOBGNGKWEFQSSG-UFXYQILXSA-N tert-butyl (2s)-2-[[3-[2-(4-fluorophenyl)ethyl]-6-[1-(4-fluorophenyl)-2-(3-methylimidazol-4-yl)ethoxy]pyridine-2-carbonyl]amino]-4-methylsulfanylbutanoate Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC(C)(C)C)=NC=1OC(C=1C=CC(F)=CC=1)CC1=CN=CN1C NOBGNGKWEFQSSG-UFXYQILXSA-N 0.000 claims description 4
• XXORVJJRUSJCKQ-JFINJBMXSA-N (2S)-2-[[2-(4-fluorophenyl)-4-[[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]methyl]benzoyl]amino]-2-methyl-4-methylsulfanylbutanoic acid Chemical compound C1=C(C=2C=CC(F)=CC=2)C(C(=O)N[C@@](C)(CCSC)C(O)=O)=CC=C1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 XXORVJJRUSJCKQ-JFINJBMXSA-N 0.000 claims description 3
• LVTBNCHEABDGJG-UFXYQILXSA-N (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[1-(4-fluorophenyl)-2-(2-methylimidazol-1-yl)ethoxy]benzoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(O)=O)=CC=1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1C LVTBNCHEABDGJG-UFXYQILXSA-N 0.000 claims description 3
• DUUGULCWUJQGRI-PMCHYTPCSA-N (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[2-(3-methylimidazol-4-yl)-1-(1,3-thiazol-2-yl)ethoxy]benzoyl]amino]-4-methylsulfonylbutanoic acid Chemical compound CN1C=NC=C1CC(C=1SC=CN=1)OC(C=C1C(=O)N[C@@H](CCS(C)(=O)=O)C(O)=O)=CC=C1CCC1=CC=C(F)C=C1 DUUGULCWUJQGRI-PMCHYTPCSA-N 0.000 claims description 3
• UYBVQPDAGMHIPE-SKCDSABHSA-N (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[2-imidazol-1-yl-1-(1,3-thiazol-2-yl)ethoxy]benzoyl]amino]-4-methylsulfonylbutanoic acid Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCS(=O)(=O)C)C(O)=O)=CC=1OC(C=1SC=CN=1)CN1C=CN=C1 UYBVQPDAGMHIPE-SKCDSABHSA-N 0.000 claims description 3
• WRFQUZLGGWMFRK-UFXYQILXSA-N (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]methyl]benzoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(O)=O)=CC=1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 WRFQUZLGGWMFRK-UFXYQILXSA-N 0.000 claims description 3
• ZAMJHJDASBFKKM-MBMZGMDYSA-N (2s)-2-[[4-[[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]methyl]-2-phenylbenzoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound C1=C(C=2C=CC=CC=2)C(C(=O)N[C@@H](CCSC)C(O)=O)=CC=C1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 ZAMJHJDASBFKKM-MBMZGMDYSA-N 0.000 claims description 3
• CJOOSJWATKWEAG-XLTVJXRZSA-N (2s)-2-[[5-[[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]methyl]-2-[(4-fluorophenyl)methyl]benzoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound C=1C=C(CC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(O)=O)=CC=1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 CJOOSJWATKWEAG-XLTVJXRZSA-N 0.000 claims description 3
• WCVIPVCRFCUNHL-UHFFFAOYSA-N 2-[[2-(4-fluorophenyl)-4-[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]benzoyl]amino]-4-methylsulfonylbutanoic acid Chemical compound C1=C(C=2C=CC(F)=CC=2)C(C(=O)NC(CCS(=O)(=O)C)C(O)=O)=CC=C1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1 WCVIPVCRFCUNHL-UHFFFAOYSA-N 0.000 claims description 3
• HLYXQGYLYUVREP-UHFFFAOYSA-N 2-[[2-[2-(4-fluorophenyl)ethyl]-5-[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]benzoyl]amino]-4-methylsulfonylbutanoic acid Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)NC(CCS(=O)(=O)C)C(O)=O)=CC=1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1 HLYXQGYLYUVREP-UHFFFAOYSA-N 0.000 claims description 3
• GNCQFLOFIAFFTL-FSRLHOSWSA-N C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC)=CC=1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC)=CC=1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 GNCQFLOFIAFFTL-FSRLHOSWSA-N 0.000 claims description 3
• BLURAXNMSNNGFB-XLTVJXRZSA-N COC(=O)[C@H](CCSC)NC(=O)c1ccc(COC(Cn2ccnc2)c2ccc(F)cc2)cc1-c1ccccc1 Chemical compound COC(=O)[C@H](CCSC)NC(=O)c1ccc(COC(Cn2ccnc2)c2ccc(F)cc2)cc1-c1ccccc1 BLURAXNMSNNGFB-XLTVJXRZSA-N 0.000 claims description 3
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
• XRZHBTDCICDNFF-CDRRMRQFSA-N cyclopentyl (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]benzoyl]amino]-4-methylsulfanylbutanoate Chemical compound N([C@@H](CCSC)C(=O)OC1CCCC1)C(=O)C(C(=CC=1)CCC=2C=CC(F)=CC=2)=CC=1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1 XRZHBTDCICDNFF-CDRRMRQFSA-N 0.000 claims description 3
• LBYPMZOILCKYPU-VQSVVBPOSA-N methyl (2s)-2-[[2-(4-fluorophenyl)-4-[[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]methyl]benzoyl]amino]-2-methyl-4-methylsulfanylbutanoate Chemical compound C1=C(C=2C=CC(F)=CC=2)C(C(=O)N[C@@](C)(CCSC)C(=O)OC)=CC=C1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 LBYPMZOILCKYPU-VQSVVBPOSA-N 0.000 claims description 3
• DHIPYZIJFFUFIQ-SKCDSABHSA-N methyl (2s)-2-[[2-(4-fluorophenyl)-4-[[2-imidazol-1-yl-1-(1,3-thiazol-2-yl)ethoxy]methyl]benzoyl]amino]-4-methylsulfanylbutanoate Chemical compound C1=C(C=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC)=CC=C1COC(C=1SC=CN=1)CN1C=CN=C1 DHIPYZIJFFUFIQ-SKCDSABHSA-N 0.000 claims description 3
• YYPXVKFAIGMQRQ-QBHOUYDASA-N methyl (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[2-(4-methylimidazol-1-yl)-1-(1,3-thiazol-2-yl)ethoxy]benzoyl]amino]-4-methylsulfanylbutanoate Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC)=CC=1OC(C=1SC=CN=1)CN1C=NC(C)=C1 YYPXVKFAIGMQRQ-QBHOUYDASA-N 0.000 claims description 3
• MARNSKLUMALPBI-CDRRMRQFSA-N n-[(2s)-1-[(4-chlorophenyl)sulfonylamino]-4-methylsulfanyl-1-oxobutan-2-yl]-2-(4-fluorophenyl)-4-[[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]methyl]benzamide Chemical compound N([C@@H](CCSC)C(=O)NS(=O)(=O)C=1C=CC(Cl)=CC=1)C(=O)C(C(=C1)C=2C=CC(F)=CC=2)=CC=C1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 MARNSKLUMALPBI-CDRRMRQFSA-N 0.000 claims description 3
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• TUJLLKHPLSHPEY-UFXYQILXSA-N tert-butyl (2s)-2-[[2-(4-fluorophenyl)-4-[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]benzoyl]amino]-4-methylsulfanylbutanoate Chemical compound C1=C(C=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(=O)OC(C)(C)C)=CC=C1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1 TUJLLKHPLSHPEY-UFXYQILXSA-N 0.000 claims description 3
• YQCXLNJPRSEEIO-CYZZXXEPSA-N tert-butyl (2s)-2-[[2-(4-fluorophenyl)-4-[[1-(4-fluorophenyl)-2-(3-methylimidazol-4-yl)ethoxy]methyl]benzoyl]amino]-4-methylsulfonylbutanoate Chemical compound CN1C=NC=C1CC(C=1C=CC(F)=CC=1)OCC1=CC=C(C(=O)N[C@@H](CCS(C)(=O)=O)C(=O)OC(C)(C)C)C(C=2C=CC(F)=CC=2)=C1 YQCXLNJPRSEEIO-CYZZXXEPSA-N 0.000 claims description 3
• LEBDHCYUIHLTKY-CYZZXXEPSA-N tert-butyl (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]benzoyl]amino]-4-methylsulfonylbutanoate Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCS(C)(=O)=O)C(=O)OC(C)(C)C)=CC=1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1 LEBDHCYUIHLTKY-CYZZXXEPSA-N 0.000 claims description 3
• IAQBZOGJDNVYKS-MBMZGMDYSA-N tert-butyl (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[2-imidazol-1-yl-1-(1,3-thiazol-2-yl)ethoxy]benzoyl]amino]-4-methylsulfonylbutanoate Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCS(C)(=O)=O)C(=O)OC(C)(C)C)=CC=1OC(C=1SC=CN=1)CN1C=CN=C1 IAQBZOGJDNVYKS-MBMZGMDYSA-N 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• ZDODLNXUFCADGK-MBMZGMDYSA-N (2s)-2-[[2-(4-fluorophenyl)-4-[[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]methyl]benzoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound C1=C(C=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(O)=O)=CC=C1COC(C=1C=CC(F)=CC=1)CN1C=CN=C1 ZDODLNXUFCADGK-MBMZGMDYSA-N 0.000 claims description 2
• HAHLCOMVMYTOAN-UXMRNZNESA-N (2s)-2-[[2-(4-fluorophenyl)-4-[[2-imidazol-1-yl-1-(1,3-thiazol-2-yl)ethoxy]methyl]benzoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound C1=C(C=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(O)=O)=CC=C1COC(C=1SC=CN=1)CN1C=CN=C1 HAHLCOMVMYTOAN-UXMRNZNESA-N 0.000 claims description 2
• FHAGHUIKYTYKRN-XLTVJXRZSA-N (2s)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[1-(4-fluorophenyl)-2-imidazol-1-ylethoxy]benzoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound C=1C=C(CCC=2C=CC(F)=CC=2)C(C(=O)N[C@@H](CCSC)C(O)=O)=CC=1OC(C=1C=CC(F)=CC=1)CN1C=CN=C1 FHAGHUIKYTYKRN-XLTVJXRZSA-N 0.000 claims description 2
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